Silvestri debuted in 1994, releasing his eponymous album. The set received a Targa Tenco for Best Debut Album. In 1995, he competed in the Newcomers' Section of the Sanremo Music Festival with the song "L'uomo col megafono". The track was included in his second studio album, Prima di essere uomo, whose second single, "Le cose che abbiamo in comune", became a radio hit in 1995 and received the Targa Tenco for Song of the Year.